Araliphatic sulfonium and their use

• US 5,247,113 A
• Filed: 01/07/1991
• Issued: 09/21/1993
• Est. Priority Date: 01/16/1989
• Status: Expired due to Fees

• Current Assignee: Huntsman Advanced Materials Americas, Inc.
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Roth, Martin, Muller, Beat
• Primary Examiner(s): Shaver, Paul F.
• Assistant Examiner(s): Nazario, Porfirio
• Application Number:
  US07/638,602
• Time in Patent Office: 988 Days
• Field of Search: 556/64, 568/18, 568/77
• US Class Current: 556/64
• CPC Class Codes: C07C 381/12 Sulfonium compounds
• CPC Class Codes: C08G 59/687 containing sulfur

Abstract

Sulfonium salts of the formulae I to IV ##STR1## in which A is C₁ -C₁₂ alkyl, C₃ -C₈ cycloalkyl, C₄ -C₁₀ cycloalkylalkyl, phenyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, Ar, Ar¹ and Ar², independently of one another, are each unsubstituted or mono- or polysubstituted phenyl, or naphthyl which is unsubstituted or mono- or polysubstituted each arylene is an unsubstituted or mono- or polysubstituted phenylene or unsubstituted or mono- or polysubstituted naphthylene and Q.sup.⊖ is SbF₆^-, AsF₆^- or SbF₅ OH^- are valuable curing agents and curing accelerators in the heat-curing of cationically polymerizable compounds, preferably epoxy resins.

Claims

1. A sulfonium salt of the formula I, II, III or IV ##STR11## in which A is C₁ -C₁₂ alkyl, C₃ -C₈ cycloalkyl, C₄ -C₁₀ cycloalkylalkyl, phenyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, Ar, Ar¹ and Ar², independently of one another, are each phenyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms or is naphthyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, each arylene is phenylene which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C.sub. 4 alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms or naphthylene which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms and Q.sup.⊖

is SbF₆^-, AsF₆^- or SbF₅ OH^-.

2. A sulfonium salt of the formula I or II according to claim 1, in which A is C₁ -C₁₂ alkyl, C₃ -C₈ cycloalkyl, C₄ -C₁₀ cycloalkylalkyl, phenyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, Ar, Ar¹ and Ar², independently of one another, are each phenyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, or is naphthyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, and Q.sup.⊖

is SbF₆^-, AsF₆^- or SbF₅ OH^-.

3. A sulfonium salt of the formula I or II according to claim 1, in which A is C₁ -C₁₂ alkyl or phenyl which is unsubstituted or substituted by halogen or C₁ -C₄ alkyl, Ar, Ar¹ and Ar², independently of one another, are each phenyl which is unsubstituted or mono- or polysubstituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, Cl or Br and Q.sup.⊖

is SbF₆^- or SbF₅ OH^-.

4. A sulfonium salt of the formula II according to claim 1, in which Ar, Ar¹ and Ar², independently of one another, are each phenyl which is unsubstituted or substituted by C₁ -C₈ alkyl, C₁ -C₄ alkoxy, Cl or Br and Q.sup.⊖

is SbF₆^- or SbF₅ OH^-.

5. Tribenzylsulfonium hexafluoroantimonate, tris(p-methylbenzyl)sulfonium hexafluoroantimonate, tris(p-chlorobenzyl)sulfonium hexafluoroantimonate and dibenzylphenylsulfonium hexafluoroantimonate.